Vitamin B12 and hydrogen atom transfer cooperative catalysis as a hydride nucleophile mimic in epoxide ring opening

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dc.citation.articleNumber101372en_US
dc.citation.issueNumber4en_US
dc.citation.journalTitleCell Reports Physical Scienceen_US
dc.citation.volumeNumber4en_US
dc.contributor.authorFunk, Brian E.en_US
dc.contributor.authorPauze, Martinen_US
dc.contributor.authorLu, Yen-Chuen_US
dc.contributor.authorMoser, Austin J.en_US
dc.contributor.authorWolf, Gemmaen_US
dc.contributor.authorWest, Julian G.en_US
dc.date.accessioned2023-05-02T14:43:13Zen_US
dc.date.available2023-05-02T14:43:13Zen_US
dc.date.issued2023en_US
dc.description.abstractEpoxide ring-opening reactions have long been utilized to furnish alcohol products that are valuable in many subfields of chemistry. While many epoxide-opening reactions are known, the hydrogenative opening of epoxides via ionic means remains challenging because of harsh conditions and reactive hydride nucleophiles. Recent progress has shown that radical chemistry can achieve hydrogenative epoxide ring opening under relatively mild conditions; however, these methods invariably require oxophilic metal catalysts and sensitive reagents. In response to these challenges, we report a new approach to epoxide ring-opening hydrogenation using bio-inspired Earth-abundant vitamin B12 and thiol-centric hydrogen atom transfer (HAT) co-catalysis to produce Markovnikov alcohols under visible light irradiation. This powerful reaction system exhibits a broad substrate scope, including a number of electrophilic and reductively labile functionalities that would otherwise be susceptible to reduction or cleavage by hydride nucleophiles, and preliminary mechanistic experiments are consistent with a radical process.en_US
dc.identifier.citationFunk, Brian E., Pauze, Martin, Lu, Yen-Chu, et al.. "Vitamin B12 and hydrogen atom transfer cooperative catalysis as a hydride nucleophile mimic in epoxide ring opening." <i>Cell Reports Physical Science,</i> 4, no. 4 (2023) Cell Press: https://doi.org/10.1016/j.xcrp.2023.101372.en_US
dc.identifier.digital1-s2-0-S2666386423001406-mainen_US
dc.identifier.doihttps://doi.org/10.1016/j.xcrp.2023.101372en_US
dc.identifier.urihttps://hdl.handle.net/1911/114859en_US
dc.language.isoengen_US
dc.publisherCell Pressen_US
dc.rightsThis is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).en_US
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/).en_US
dc.titleVitamin B12 and hydrogen atom transfer cooperative catalysis as a hydride nucleophile mimic in epoxide ring openingen_US
dc.typeJournal articleen_US
dc.type.dcmiTexten_US
dc.type.publicationpublisher versionen_US
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